Transform Your Sales Team: Strategic Compensation Adjustments for Year-End Momentum

Transform Your Sales Team: Strategic Compensation Adjustments for Year-End Momentum

Autumn is the time of year for sales leaders, managers, and CEOs to begin laying the groundwork for next year’s success. Have you considered how your current sales compensation plans impact your team’s motivation and productivity? Now is the ideal moment to evaluate, adjust, and deliver these plans, preferably by December 1st. Doing so can significantly influence your team’s drive to close deals in December and build momentum heading into the next fiscal year.

Sales compensation should be motivating and rewarding for employees. It directly shapes your sales team’s behaviors and priorities. An effective plan incentivizes the right actions and deters the wrong ones.

Consider a common pitfall: salespeople holding back deals to inflate their numbers for the following year. Does your current compensation structure inadvertently reward this practice? If so, you’re unintentionally harming your year-end results.

To counter this, strategically incorporate compensation escalators and cliffs into your plan. Escalators progressively reward increased sales performance throughout the year. Higher performance equals higher commission rates, driving your sales team to push forward continually. 

Commission cliffs reset commission rates at the beginning of each year, creating a sense of urgency to close deals before the end of December. Communicating these compensation details clearly by early December ensures your team understands what’s at stake.

Don’t hold your team back!

Another critical compensation consideration is eliminating commission caps. While some organizations cap commissions to control expenses, this practice can backfire dramatically. Caps tell your top-performing salespeople that their exceptional efforts are neither valued nor rewarded appropriately. This demotivates your top talent and encourages them to seek opportunities elsewhere that offer uncapped rewards. 

Removing commission caps signals that the organization fully supports and rewards outstanding performance. Have you considered how much growth your company might achieve if artificial constraints didn’t limit your sales team?

When evaluating compensation, look beyond simple cost containment. Consider the true profitability of incentivizing increased sales volume. Once salespeople reach their targets and enter accelerators, each additional dollar earned typically comes at a lower incremental cost to your organization. 

Sales transactions earlier in the year have already covered the salesperson’s base salary once they have met their annual quota. In fact, at 100% of quota, the salesperson should have covered all their costs and their share of the overall company’s revenue needs. Thus, every extra sale at escalated commission rates still contributes positively to your overall profitability. 

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Two Tall Guys Talking Sales – How Sales Leaders Use CRMs to Align Sales Processes, Value Selling, and Revenue Management – Episode 152

Two Tall Guys Talking Sales – How Sales Leaders Use CRMs to Align Sales Processes, Value Selling, and Revenue Management – Episode 152

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey build on last week’s discussion of qualification methodologies and take the conversation further—into how these frameworks should live inside your CRM. From aligning sales processes with the buyer’s journey to enforcing accountability at each stage, this conversation offers practical strategies that every sales leader and salesperson can implement. Expect a deep dive into sales management, revenue generation, sales processes, and how value selling thrives when marketing and sales teams work in sync.

Key Topics Discussed

  • Why your CRM is the right home for qualification methodologies (00:48)
  • Best practices for embedding qualification questions into sales processes (02:01)
  • How sales leaders enforce discipline and consistency across teams (03:18)
  • Eliminating Excel spreadsheets and consolidating data for effective revenue management (05:12)
  • Aligning marketing collateral with sales strategies to support qualification and value selling (06:00)
  • Real-world stories of late-stage deal failures caused by missing buyer-side approvals (10:21)

Key Quotes

  • Kevin Lawson (05:12): “Oh, please, oh, please evacuate Excel spreadsheets from your solution guide… For the purposes of this discussion, we want to strenuously avoid having third-party apps disconnected from your system.”
  • Sean O’Shaughnessey (10:40): “There is nothing worse than missing your quarterly number because you didn’t know how they were going to buy… Knowing the paperwork process is the difference between celebrating the win and missing your commission check.”
  • Kevin Lawson (14:10): “Having a qualification methodology mapped into your CRM, aligned with a buyer’s journey and supported by marketing resources, gives you a fully wrapped system that prevents that dreaded CEO call asking, ‘What’s the status of that deal?’”

Additional Resources

A Significant Actionable Item from this Podcast

Embed your qualification methodology directly into your CRM, tied to each stage of your sales process.

Don’t let critical deal information reside inside spreadsheets or Word docs; configure your CRM so progression requires those qualification questions to be answered. This not only improves sales accuracy but also enhances revenue management, ensures consistency across your team, and creates alignment with marketing resources to drive value selling.

Summary

This episode of Two Tall Guys Talking Sales is a must-listen for anyone serious about building sustainable sales success. Sean and Kevin reveal how sales strategies such as qualification methodologies come to life when fully integrated into CRM-driven sales processes. You’ll learn why sales management must prioritize data consistency, how business acumen prevents late-stage deal disasters, and how aligning messaging between sales and marketing fuels stronger revenue generation. If you want practical insights on improving your sales processes and elevating your organization’s performance, download this episode today and start putting these best practices to work.

Transforming Quota-Setting: Strategies for Sales Leaders to Optimize Performance and Revenue

Transforming Quota-Setting: Strategies for Sales Leaders to Optimize Performance and Revenue

Quota-setting is one of the most misunderstood elements of sales leadership. Too often, it’s treated as a spreadsheet exercise or a top-down directive, rather than a strategic lever that drives behavior, performance, and growth.

Whether you’re leading a team of 20 or you’re the founder managing three reps, how you define quotas has a direct impact on your revenue trajectory and your team’s motivation.

So, where do you start?

With timing. If you’re not delivering quotas to your team until February or March, you’re already behind. Salespeople need clarity by December. That gives them runway to plan, prioritize, and hit the ground running in January. Delayed quotas create confusion and stall momentum. To achieve a strong Q1, you need to equip your team early.

Quota-setting varies depending on the size of your company. Larger teams offer more flexibility. With 10 or more reps, you can spread risk, balance performance, and model averages. You’ll have top performers who consistently overdeliver, alongside newer reps who are still ramping up. The law of averages works in your favor. You can afford some variance. Smaller teams don’t have that luxury.

When you’re running a small team, maybe two or three reps or founder-led sales, every individual matters. One person missing quota can tank your number.

You can’t rely on averages. You need precision.

That means tying quotas to actual relationships, known opportunities, and real probability. It’s not about slicing up a target evenly. It’s about assigning numbers based on what’s realistically achievable in each territory or account list.

Territory design plays a big role here. Whether it’s geographic, vertical, or named accounts, quota must reflect the market potential. You can’t expect equal performance from unequal opportunity. If Rep A has 500 viable accounts and Rep B has 50, their quotas shouldn’t look the same unless you have data that says Rep B’s accounts are closer to your Ideal Client Profile. Use available market data to inform the number. Don’t assign quotas in a vacuum. 

In larger organizations, quotas often originate from the top down, typically from finance. The CEO and CFO commit a growth number to the board, investors, or in public filings to the SEC. They have no choice but to pass it down. It’s not uncommon for the sales team to receive the number without context. That’s a problem. If you’re in a leadership role, you need to pressure test that number. Can your team realistically hit it? If not, what additional resources are required?

  • More headcount?
  • Better enablement?
  • Marketing support?

In large organizations where the quota is driven by investor expectations, the VP of Sales must establish an organization well before the new year that achieves this year’s goal, while also meeting the expectation of growth for the next year. Planning ahead, sometimes years in advance, is part of the job.

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Two Tall Guys Talking Sales – Building a Sales Powerhouse—The 3 Most Underrated Skills with Jeff Parris – Episode 143

Two Tall Guys Talking Sales – Building a Sales Powerhouse—The 3 Most Underrated Skills with Jeff Parris – Episode 143

Sales isn’t about persuasion but service, resilience, and growth. In this episode of Two Tall Guys Talking Sales, co-hosts Kevin Lawson and Sean O’Shaughnessey welcome sales leader and former professional athlete Jeff Parris to explore the fundamental skills that separate elite salespeople from the rest. Drawing on decades of experience, Jeff shares three often-overlooked yet foundational competencies that drive sales success, and they’re not what you’d expect. Whether you’re a VP of Sales building a high-performance team or a seller looking to level up, this episode delivers sharp insights on value selling, business acumen, and sales management excellence.

Key Topics Discussed

  • Why great salespeople see themselves as servants first (approx. 04:00)
    Jeff outlines why a “motivation to serve” mindset creates stronger client relationships and more consistent revenue generation.
  • Ego Drive vs. Ego Trip: Understanding the will to win without arrogance (approx. 07:30)
    Learn how ego drive, a hunger to persuade for the buyer’s benefit, builds durable sales performance.
  • Curiosity as the gateway to sales mastery (approx. 10:15)
    Jeff and Sean dig into why curiosity fuels continuous improvement and business acumen across every sales process.
  • How to coach the “accidental salesperson” into a top performer (approx. 11:45)
    Kevin asks how people without formal sales backgrounds can thrive by developing the right mindset.
  • Sales leaders as talent architects: Building high-performance teams (approx. 02:00)
    Jeff draws on his athletic past to share what makes a sales team championship-worthy.

Key Quotes

  • “Sales isn’t something we do to people, it’s something we do for people.”
    — Jeff Parris (04:00)
  • “The real goal of a great salesperson is: ‘Mr. Prospect, let me help you solve that problem.”
    — Sean O’Shaughnessey (05:55)
  • “Having the right people, with the right skills, in the right seats makes winning so much easier.”
    — Kevin Lawson (03:36)
  • “Curiosity leads to better solutions. Every interaction is a chance to learn and improve your craft.”
    — Jeff Parris (10:50)

Additional Resources

A Significant Actionable Item from this Podcast

Evaluate your team (and yourself) on the “Service–Drive–Curiosity” Triad.
Start by asking three questions:

  1. Does this salesperson show a genuine desire to serve the customer’s goals?
  2. Do they take pride in persuading with purpose, not just for commission but impact?
  3. Are they consistently seeking to learn more about the customer, the industry, and their performance?

Use these questions in your next 1-on-1 or team coaching session to align your talent strategy with the kind of sales success that sustains revenue generation.

Why You Should Listen to This Episode

If you’re tired of surface-level sales advice, this conversation will challenge your thinking and expand your toolkit. Jeff Parris brings clarity, conviction, and humility to what it means to lead with purpose in today’s complex B2B landscape. From building elite sales teams to refining your individual sales strategy, this episode is packed with practical wisdom for leaders, sellers, and anyone serious about mastering the craft of sales. Tune in now and discover the underestimated traits that drive extraordinary outcomes.

Two Tall Guys Talking Sales – From Regular Season to Postseason: Coaching Your Sales Team to Win – E128

Two Tall Guys Talking Sales – From Regular Season to Postseason: Coaching Your Sales Team to Win – E128

As a sales leader, are you coaching your team for the long haul, or are you scrambling in the final weeks of the quarter? In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey break down the difference between regular season and postseason play—whether in sports or sales. They explore why last-minute Hail Mary strategies can be damaging, how to manage time, and the importance of effective and consistent coaching. With March Madness and The Masters as the backdrop, this conversation is packed with insights to help you refine your sales approach and ensure your team is always in winning form.

Key Topics Discussed

  • The Sales Tournament Mentality (00:02:00) – What sales teams can learn from March Madness and The Masters, and why only one team wins while the rest lose.
  • Building a Winning Sales Team (00:03:30) – How business owners can prepare their sales teams to perform under pressure by ensuring the right people are in the right seats.
  • The Role of Sales Coaching (00:05:00) – Why sales leaders must incorporate skills development into every sales meeting instead of just reviewing the pipeline.
  • The Pitfalls of End-of-Quarter Desperation (00:07:50) – How last-minute discounting and rushed deals create long-term problems and train customers to buy at a discount.
  • Mastering Time Management in Sales (00:10:00) – How prioritization and disciplined execution throughout the quarter prevent last-minute chaos and boost consistent performance.

Key Quotes

  • Kevin Lawson (00:07:53): “If you’re behind in sales right now, don’t throw Hail Marys. Don’t discount. You’re teaching your prospects to wait until the end of the quarter for a better deal—and that’s a losing game.”
  • Sean O’Shaughnessey (00:13:00): “You have one thing in sales you can never get back: time. If you wasted today, it’s gone forever. You can’t go back and fix it.”
  • Kevin Lawson (00:09:00): “Salespeople with commission breath stink. If your only focus is closing the deal before Friday, your prospects will smell it a mile away—and that’s not how you build relationships.”

A Significant Actionable Item from this Podcast

Develop a Five-Week Sales Training Plan – Sales leaders should map out the next five sales meetings, dedicating at least five minutes to skills development in each session. Focus on topics such as pipeline progression, prospect qualification, and closing techniques. Training should not be an afterthought—it should be a fundamental part of your sales strategy.

Why You Should Listen to This Episode

Whether you’re a sales leader or a frontline salesperson, this episode is your playbook for maintaining momentum all year long. Avoid the common traps of end-of-quarter desperation, build a disciplined approach to sales training, and master the art of time management. Just like in sports, sales success isn’t about last-minute heroics—it’s about consistent execution.

Tune in now and take your sales game to the next level!

Two Tall Guys Talking Sales – The Motivation Formula: Achieving Big Wins in Sales – E116

Two Tall Guys Talking Sales – The Motivation Formula: Achieving Big Wins in Sales – E116

In this compelling episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the heart of sales motivation and goal setting. They share relatable stories, actionable insights, and practical strategies for salespeople and sales leaders. Using a vivid sports analogy, Sean sets the tone for an episode packed with strategies to stay driven—even when the path isn’t clear. Whether you’re grappling with setting goals or maximizing your commission potential, this episode is a goldmine for actionable advice and personal growth.

Key Topics Discussed

  • The Athlete Analogy: Personal Motivation Meets Team Success (0:00)
    Sean parallels a high school sprinter’s rigorous training and the dedication needed to succeed in sales.
  • The Importance of Personal “Why” in Sales Motivation (6:00)
    Kevin and Sean explore how individual motivations—whether financial goals, family obligations, or personal growth—shape sales performance.
  • Breaking Down Your Sales Math to Achieve Success (10:00)
    Kevin explains how to reverse-engineer your earnings goal, calculate deal requirements, and align your activities with desired outcomes.
  • Creating Personal Rewards for Milestone Achievements (9:00)
    Sean shares a story about a salesperson’s unique approach to celebrating significant deals and how small rewards can drive consistent motivation.
  • The Art of Setting Goals When None Are Provided (3:30)
    Kevin and Sean discuss practical steps for creating your own sales targets when your organization hasn’t assigned any.

Key Quotes

  • Sean O’Shaughnessey (2:00):
    “What motivates you as a salesperson to do incredibly well? What are you doing to achieve your goals, and because you achieve your goals, maybe you’re inspiring someone else on your team to do the same.”
  • Kevin Lawson (4:29):
    “If you’re not given a goal, do the math that gets you to success. It starts with understanding your economic driver and building a plan from there.”
  • Sean O’Shaughnessey (9:20):
    “Choose something unique to reward yourself when something good happens. It’s a motivator for the day and can become the beginning of your career motivation.”

A Significant Actionable Item from this Podcast
Reverse-engineer your sales goals for 2024. Start by defining your desired income, break it down into weekly targets, and calculate how many deals you need to close. Then, analyze your closing rates to determine how many leads and opportunities you need to generate. Finally, track your progress weekly and adjust your strategy to stay on course.

Summary Paragraph
This episode of Two Tall Guys Talking Sales delivers powerful insights into staying motivated and setting actionable sales goals. Sean and Kevin expertly weave relatable analogies with proven strategies to help you master the art of self-motivation and goal achievement. Whether you’re working towards a personal milestone or aiming to inspire your team, this episode provides the tools to elevate your performance. Tune in and take control of your sales journey today!

Building a Successful Sales Team: A Guide for CEOs and Managers

Building a Successful Sales Team: A Guide for CEOs and Managers

You can overcome obstacles and significantly improve your sales performance with the right mindset, strategies, and tools. For salespeople, sales managers, and CEOs of small companies, the journey to sales excellence is paved with lessons and insights that can be invaluable in improving management capabilities and driving revenue growth.

The sales process is a critical aspect of any business. It’s the engine that drives revenue and growth and the platform on which customer relationships are built. However, businesses often encounter a unique problem in their sales process. The problem isn’t necessarily about the product or service being sold, the market, or the competition. Rather, it’s about the people involved in the process—the salespeople.

Being a salesperson is a challenging profession. It requires a unique set of skills, a deep understanding of the product or service being sold, and a certain level of resilience to face the inevitable rejections that come with the job. But more than that, it requires a mindset that embraces growth, learning, and continuous improvement.

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Designing Sales Compensation Plans That Drive Performance

Designing Sales Compensation Plans That Drive Performance

The success of any sales-driven organization in the business-to-business (B2B) space hinges on the sales team’s compensation plan. Over my four decades in B2B sales, I’ve observed that nothing influences the performance of sales personnel more directly than the design and implementation of their compensation plans. Compensation is not merely about rewarding sales achievements but crafting a strategy aligning individual salespeople’s goals with the company’s broader objectives.

A well-structured compensation plan acts as both a motivator and a guide. It compels sales teams not only to meet but exceed their targets, fostering an environment where continuous improvement is not just encouraged but becomes a natural byproduct of the system. For small business CEOs, understanding this dynamic is critical for sustaining and driving growth. Sales compensation is more than just a cost; it’s an investment in the company’s future.

In any sales environment, whether the market is brimming with potential or tightly contested, the compensation plan must be a living document that evolves in response to market conditions, company goals, and team performance. With this adaptability, companies can avoid stagnation or regression in their market positions. As businesses strive to scale and adapt, constructing a compensation plan that genuinely drives the right behaviors becomes all the more pertinent.

To delve deeper into this vital subject, CEOs should consider the immediate impacts of their compensation strategies and their long-term implications on sales culture and employee retention. For those ready to explore the intricacies of effective sales compensation and ensure their strategies are well-suited to their specific business contexts, I am here to lend my expertise. With extensive experience tailoring compensation plans to enhance sales productivity and company profitability, I invite you to reach out for further guidance on crafting a plan that meets and exceeds your strategic goals. You can set a time to talk to me using my link above Book Appointment With Sean.

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Optimizing Sales Territories for Growth and Efficiency

Optimizing Sales Territories for Growth and Efficiency


Territory design is critical for ensuring efficient revenue generation and optimal team performance. Sales leaders, especially those at the helm of small—to mid-sized companies, must revisit and potentially recalibrate their territory strategies to accommodate growth and maintain competitiveness.

Effective territory management starts with a clear understanding of the business landscape. Ensuring that each salesperson has a viable area with ample opportunity is crucial. This may sound straightforward but involves a delicate balance of geographic and customer-based considerations. For instance, some businesses might operate on a model where territories are defined by customer types or specific named accounts, which could include focusing on a set number of businesses to target. On the other hand, more geographically expansive businesses might allocate territories based on regions, such as counties or states, depending on their size and scope.

Moreover, there’s an art to knowing when and how to split or expand territories without diluting the quality of customer relationships or the sales team’s morale. For example, if a territory becomes too large and unwieldy, it might necessitate division to maintain or increase effectiveness. However, this division must be approached with sensitivity and strategy, ensuring it does not merely become a means to reduce commission costs but rather a method to enhance coverage and customer engagement.

The challenge often lies in the execution. Realigning territories can be as complex as managing a new product launch or entering a new market. Factors such as supply chain logistics, warranty services, and resource allocation must all be considered to ensure the new territory design supports immediate sales goals and long-term business growth.

Sales leaders must also be adept at navigating the internal dynamics of territory adjustments. For instance, a well-performing salesperson might view the reduction of their territory as a punitive measure, rather than an opportunity to enhance focus and potentially increase earnings from a more concentrated area. It is crucial for management to communicate effectively, ensuring that the team understands these changes are aimed at optimizing the entire sales process and enhancing their ability to meet customer needs more effectively.

Ultimately, the goal of territory design should align with the overarching business strategy aimed at growth and sustainability. This includes not only deciding the physical or conceptual boundaries of each territory but also ensuring that each sales team member is positioned to succeed, supported by robust training and resources, and motivated by a clear understanding of their role in the company’s broader objectives.

As companies prepare for another business cycle, revisiting the principles of effective territory management could be the key to unlocking new levels of success and stability. This strategic approach helps maintain a competitive edge and supports a healthy, dynamic sales culture that adapts to the changing landscapes of industries and markets.

Actionable suggestions that sales managers can do today:

  1. Conduct a Territory Audit: Review your current sales territories by evaluating sales data, customer distribution, and team feedback. Identify areas where territories may be too large or too small and assess the potential for restructuring to improve coverage and salesperson efficiency. This will help you understand if your current design aligns with optimal market coverage and team capabilities.
  2. Initiate a Team Discussion: Meet your sales team to discuss the current territory alignment. Use this opportunity to gather insights directly from those on the ground about their territories’ challenges and opportunities. This feedback is invaluable for making informed decisions about potential territory realignments or adjustments to meet customer needs and company goals.
Building High-Performing Sales Teams through Strategic Alignment

Building High-Performing Sales Teams through Strategic Alignment

The challenge of aligning the right people with the right organizational roles is paramount. As sales leaders and CEOs of small companies, understanding the intricacies of building and maintaining a proficient sales team is crucial for driving growth and achieving success.

The concept of having the “right people in the right seats” is not just a matter of recruitment but an ongoing process of evaluation, development, and strategic alignment. It’s essential to recognize that the adequacy of a sales team is not solely dependent on individual capabilities but also on how these individuals fit within the broader sales strategy and organizational culture.

Compensation plans, customer relationship management (CRM) systems, and the overarching sales infrastructure play significant roles in enabling sales teams to perform at their best. However, the foundation of a high-performing sales team lies in the continuous investment in people. This involves identifying talent and fostering an environment that promotes learning, growth, and adaptation.

Training and development are often overlooked aspects of sales management. Surprisingly, a significant number of sales professionals and leaders go years without receiving formal training. This gap in skill development can lead to stagnation and inefficiency. Therefore, organizations must prioritize ongoing education and training to keep their sales teams agile and competitive.

Furthermore, it is critical that individual roles align with the organization’s goals. This may involve reevaluating existing roles, responsibilities, and processes to ensure they contribute effectively to the sales strategy. Sometimes, the solution does not lie in hiring new talent but in optimizing the current team’s structure and roles to leverage their strengths more effectively.

Performance improvement plans (PIPs) and the concept of “top-grading” the sales team highlight the importance of accountability and continuous improvement. While PIPs can be a tool for addressing performance issues, they should not be the first resort. Instead, leaders should focus on setting clear expectations, providing the necessary resources and support, and fostering a culture of excellence.

Sometimes, the issue may not be with the sales personnel but with the systems, processes, or even the leadership approach. Before making drastic decisions, such as replacing team members, it’s worth taking a step back to assess whether the organization provides the right environment, tools, and guidance for the team to succeed.

Ultimately, building and managing an effective sales team is an intricate process that requires a balanced approach. It involves ensuring that you have the right people in place and that these individuals are equipped, motivated, and aligned with the organization’s goals. As sales leaders and managers, it’s essential to identify and address gaps, foster a culture of continuous learning and improvement, and strategically align team structures and processes to drive sales performance.

For salespeople, sales managers, and CEOs of small companies, understanding these dynamics and adopting a holistic approach to sales management can significantly enhance their team’s effectiveness and their organization’s ability to achieve its sales objectives.

Actionable items that you can do today

  1. Evaluate Your Team’s Composition: Take a moment to assess the current structure of your sales team. Identify whether each member is in the role that best suits their skills and where they can contribute the most to the team’s objectives. This could involve one-on-one discussions to understand their goals, strengths, and areas for improvement.
  2. Initiate a Training Needs Analysis: Conduct a thorough training needs analysis to identify gaps in skills and knowledge within your sales team. This should cover everything from product knowledge to sales techniques and the use of CRM systems. Based on this analysis, outline a tailored training program to address these gaps and elevate your team’s performance.
  3. Review and Adjust Compensation Plans: Analyze your current compensation and incentive structures to ensure they align with your organizational goals and sales targets. Adjustments might be necessary to better motivate your team and encourage the behaviors and outcomes you wish to see. This could mean introducing new performance bonuses, adjusting commission rates, or implementing non-monetary rewards that drive motivation.
  4. Implement a Sales Enablement Strategy: Start developing or refining your sales enablement strategy to ensure your sales team has the tools, resources, and content they need to succeed. This could involve updating sales playbooks, improving CRM processes, or investing in new sales enablement technology. The goal is to make it easier for your sales team to sell effectively and efficiently.